Sodium Thiosulfate → Tert-butyl 4-methoxy-2-oxobutanoate

HRID 1779153Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1779153
[CH3:1][O:2][CH2:3][CH2:4][C:5]1([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])SCCCS1.BrN1C(=[O:24])CCC1=O.C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>CC(C)=O.O>[CH3:1][O:2][CH2:3][CH2:4][C:5](=[O:24])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]

Komponenten

7

Edukt 4

HCID 24477Sodium ThiosulfateHCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 90060334Tert-butyl 2-(2-methoxyethyl)-1,3-dithiane-2-carboxylate

Produkt 1

HCID 90060040Tert-butyl 4-methoxy-2-oxobutanoateAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

To a solution of tert-butyl 2-(2-methoxy-ethyl)-[1,3]dithiane-2-carboxylate (1.14 g, 4.09 mmol) in acetone (23 mL) was then added water (1.14 mL), and subsequently the solution was cooled to −15° C., to which N-bromosuccinimide (NBS, 4.37 g, 24.6 mmol) was gradually added. After stirring for 30 minutes and confirming the consumption of the starting materials by TLC, to the solution was added a solution of sodium bicarbonate (1.71 g, 20.35 mmol) in water (9.0 mL), and subsequently, an aqueous solution (8 mL) of 5% sodium thiosulfate. After extraction with dichloromethane, the organic layer was washed with water, and dried over anhydrous sodium sulfate. The organic layer was filtered and the solvent was distilled off. The resulting residue was purified with SP1 (SiO2 cartridge, 10% ethyl acetate/n-hexane, Rf=0.4) to obtain tert-butyl 4-methoxy-2-oxo-butyrate (550 mg, 72% yield).

Aufarbeitung

  1. additionwas gradually added
  2. customthe consumption of the starting materials by TLC
  3. extractionAfter extraction with dichloromethane
  4. washthe organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe organic layer was filtered
  7. distillationthe solvent was distilled off
  8. customThe resulting residue was purified with SP1 (SiO2 cartridge, 10% ethyl acetate/n-hexane, Rf=0.4)

Quellen und Nachweise

ORD-Eintrag
ord-5612c14e30554c5792152794a3c0d4ba
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09266853B2

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